Freedom Seekers

Some enslaved people didn’t wait for their owners to grant them freedom legally; they took fate into their own hands and freed themselves. Sometimes those who fled were soon found and returned to their owners. Others succeeded in freeing themselves permanently. No matter the end result, constant flight attempts represented a problem for slaveholders and serious challenge to the institution. The actions of fugitives belied claims that enslaved people were content, docile and incapable of life on their own.

A disproportionate number of these fugitives came from Maryland. In the 1850 census count, the state led all others in number of escaped slaves. Scholars agree the number–279–is an undercount, as not all slaveholders who lost enslaved people reported this. In Kent County, the numbers of fugitives were even higher. Nearly seventy enslaved people fled the county in the 1850’s, about forty of them in the later months of 1855. Among them were numerous people who ran away from their College owners, nearly all members of the Board of Visitors and Governors. Some of the escapes we know little about other than a name and date. Some of the attempts were successful, others not. All speak to the desire of enslaved people to be free. 


In 1789, an advertisement appeared in the Maryland Journal and Baltimore Advertiser seeking Tom, who had run away from Simon Wilmer, near Chestertown, about December 1, 1788. A detailed description, characteristic of the era, was given of Tom. He was about eighteen, slightly over five feet tall, and had pock marks on his face from a bout with smallpox. He was described as speaking with a slight lisp and being “much addicted to drinking and pilfering.” His clothing was also included in the description. His owner offered four dollars if Tom was found in state, eight if found out of state.

Phil, 1793

Phil, about forty years old, was enslaved by donor William Embleton on his farm at Howell’s Point (near today’s Betterton). A ten-dollar reward was offered for his return in the Apollo; or Chestertown Spy. Phil was described as slender, “small-featured” and about five feet eight or nine inches tall. A description of his clothing was included in the advertisement. Embleton suggested that Phil might be found with his wife, a free woman who lived in the Quaker Neck area, or at his sister’s in Sandtown (the Queen Anne’s side of Millington).

Easter, 1793  

Easter, age forty, reported as a “very tall, masculine, black negro” was advertised as a runaway in The Chestertown Gazette (Apollo) in September. The man who claimed her, Isaac Cannell, was a member of the Board of Visitors and Governors and also a renter of College lots. Cannell explained that Easter was “very apt to stutter when asked questions she cannot immediately answer”. He offered a four-dollar reward for her return.

Abolitionist Henry Highland Garnet, shown in 1881
Henny Trusty’s manumission document, signed by Isaac Spencer, 1830.

Henry Highland Garnet and family, 1822

A boy who would become one of the nation’s most prominent anti-slavery advocates escaped with his family from another family with multiple connections to Washington College. Henry Highland Garnet was born just before Christmas in 1815 on the plantation of William Spencer. Spencer, Colonel in the Maryland Militia and president of the Maryland State Senate, was a 1790 graduate of the College. He ran a plantation called Darby near Chesterville, (then called New Market) and owned in total over eleven hundred acres of land. In 1820, he claimed twenty-four enslaved people, including fifteen men aged 14 to 44, a sizeable agricultural workforce for Kent County.

When William Spencer died in March of 1822, Garnet’s parents (then known by the name Trusty), feared the family’s separation as their master’s assets were dispersed. In April, the family–nine-year-old Henry, his parents and sister, and seven other relatives– received permission to attend a funeral. Instead they journeyed by covered wagon to Wilmington, likely by way of the Maryland Road (today Route 291), to reach the home of Underground Railroad conductor Thomas Garrett. The group remained with Garrett for one night, then split up for safety. With the help of the Pennsylvania network, the Garnets made their way to New Hope, where they remained for three years before moving to New York City. Along the way, they took on new names, partly as a spiritual rebirth, partly no doubt for safety.

It seems likely that someone local provided the family with both knowledge and practical assistance. Possibilities include local Quakers, free blacks and extended family members. There was a Quaker meeting house not far from Chesterville in Head of Chester (Millington). Although Joshua Chapel, in the nearby village of Cork Town (Morgnec), a free black church, was not founded until 1839, there may have been a congregation worshipping there from an earlier date. Additionally, Kent County records show many free black people with the last name Trusty, so it is possible that the family had free black relatives who assisted in their escape.

But the Garnet family was not safe in the North. Isaac Spencer, William Spencer’s brother and heir, spent significant resources in the next decade trying to recover the Garnets and the other enslaved people he inherited. Like his brother, Isaac Spencer had a connection to Washington College, serving on the Board of Visitors and Governors from at least 1816 until his death in 1832.

William Spencer’s probate records reveal a detailed accounting of the Spencer family’s efforts to recover the people they enslaved. While Spencer left the dispersal of his estate in the hands of his brother Isaac, he indicated that he wanted his considerable estate to be divided not only among Isaac’s children, but also with those of their brother Jervis. Several of those heirs, then, joined in trying to recapture the fugitives. One of them, William A. Spencer, had graduated from Washington College just that spring. The records show ten different requests from six members of the Spencer family, as well as several hired agents, for “expenses and charges pursuing runaway negroes and stolen horses” incurred during trips to various locations in Delaware, Pennsylvania, New Jersey, and New York, from 1822 to 1830. 

Eventually one of them found the Garnet family, by 1829 living in New York City. While Henry was overseas, working as a ship’s cabin boy, his father George labored in the city as a shoemaker. George eluded the Spencer heirs, but his daughter Eliza was taken up and jailed, yet managed to convince authorities to release her. Garnet’s mother was also discovered, but her freedom was negotiated with the help of some connections from home. Money for her purchase was provided by Israel Corse, a Quaker abolitionist born in Kent County, who now lived in New York City. James Claypoole, another Kent County resident, arranged the transaction. Claypoole was a slaveholder who eventually freed all of the people he enslaved; he was also a subscriber to the College’s founding. Elizabeth Garnet, formerly Henny Trusty, was manumitted in January, 1830. Whether the rest of the family secured their freedom legally from the Spencer family is unclear.

Henry Highland Garnet went on to become one of the most prominent and complex abolitionists of the antebellum era, his tactics constantly evolving but always based on a central idea–that black people must free themselves. Garnet’s most controversial speech, “Address to the Slaves of the United States of America”, delivered at the 1843 black national convention, called on enslaved people to rise up and take their freedom by any means necessary. Garnet did not advocate large-scale revolt, believing it likely to fail; rather, he supported a general strike among enslaved people, encouraging them to see the power their labor held. But most importantly, Garnet told the enslaved, “What kind of resistance you had better make, you must decide.”

With research contributed by Paris Young, Class of 2021, and Caroline Draper, Class of 2021. We are indebted to Amanda Tuttle-Smith of the Kent County Historical Society for her research on this story.

Charlotte, 1823  

Charlotte, held in slavery by Board Treasurer Joseph Wickes, ran away while she was hired out to a Mrs. Comegys. She was either found or returned on her own, because she was hired out the following year to College President Timothy Clowes. (See Presidents) Charlotte does not appear again in Wickes’s hiring accounts. However, records document Wickes paying fellow Board member Dr. Benjamin F. Houston for medical treatment for a slave named Charlotte. This may or may not the same Charlotte who tried to free herself in 1823.

Deborah, 1842

The Kent News of August 6, 1842, reported that Deborah, aged about twenty-four, belonging to the estate of George W. Thomas, had run away the previous month. Thomas, a Board member since 1822, had died in March. He was the owner of several properties in the area, including one called Upper Farm, rented at the time to an Edward Hartley. Deborah had been hired out previously. At the time of her escape a thirty-dollar reward was offered. According to Thomas’s probate inventory Deborah was to be freed the first day of 1844; she may have feared a new owner would not honor this agreement. It is not known whether Deborah’s escape was successful. 

Jim, 1828  

When Jim ran away from Board President Ezekiel Chambers, the slaveholder wrote to his brother-in-law and law partner Joseph Wickes to ask for help in recovering his enslaved man. Jim appears to have left on New Year’s Eve, according to Chambers’s letter. The holiday season was a common time for enslaved people to leave, as they could be given time off between Christmas and New Year’s, sometimes even receive permission to visit family living at a distance. Chambers seemed confident that Jim would be found, suggesting that he knew or believed Jim had remained in the area. His next letter to Wickes reveals that Jim in fact had been found and that Chambers planned to sell him: “I am glad to hear you have put master Jim into safe quarters. He is a great rascal and I shall be pleased to get rid of him on almost any terms.”

David Freeman, 1850

In 1850, another person Chambers held to forced labor attempted to escape. Like Jim, David Freeman was also unsuccessful in his effort. Freeman was captured and jailed, held on the charge of “running away from his master against his consent with a view to escape from servitude and thereby to deprive said master of his services”. In two letters to Joseph Wickes in early 1850, Chambers explained the help he required from his law partner. In the first letter, he sought a southern buyer for Freeman, writing, “I take it for granted the price of cotton has occasioned a rise in price [in slaves] in addition to the destruction of many slaves in the South by cholera.” In the next letter Chambers explains his strategy to move the sale process along quickly and rid himself of a troublesome slave. A potential buyer, whom Chambers apparently knew, suggested Chambers intervene with the Governor to have the case dropped. This was apparently done that day; David Freeman was released from jail, pardoned for his crime, then sold out of the state.

Harriet Shephard
and family, 1855  

The news “must have produced a shock, scarcely less stunning than an earthquake.” This was how abolitionist William Still imagined the reaction to the escape of Harriet Shephard, her five children, aunt, uncle, and three other enslaved people from Chestertown in October, 1855. The Shephard family’s experience was unusual–the majority of fugitives were young, unattached, and male. But something unusual was happening in Kent County–nearly seventy people fled from slavery in the 1850’s, about forty of them in the later months of 1855.

Who held in the Shephard family in slavery is not completely clear. Two modern sources name Washington College Board member George W.T. Perkins, citing as evidence the 1860 Slave Schedule in which Perkins listed five fugitives. But evidence also points to Perkins’s father-in-law and fellow Board member, Ezekiel F. Chambers. In the 1864 Record of Slaves, Chambers listed 57 slaves, including five matching the names and possible ages of the Shephard children. Although there is no Harriet listed, there is a “Hetty” of an appropriate age. One possibility is that the Shephards were owned by Chambers but were hired out or informally loaned to Perkins at the time of their escape. 

Leaving the night of the night of October 26, the group made its way north with the help of two carriages, traveling along an established Underground Railroad route to the station of Thomas Garrett in Wilmington. Garrett sent them on to Longwood, Pennsylvania, while he used the horses they had left to distract the men who arrived searching for them. As these men kept watch on Garrett’s house, the fugitives were able to travel through southeastern Pennsylvania to Graceanna Lewis’s station in Kimberton, Chester County. There, Lewis separated the group, sending Shephard and her children into upstate New York, bound for St. Catharines, Ontario.

First, though, they were all interviewed in Philadelphia by William Still of the Pennsylvania Anti-Slavery Society. One of three young men who traveled with the Shephards, sixteen-year-old William Thomas Freeman, had taken on the alias Ezekiel Chambers, further evidence of Chambers’s connection to the group. Freeman gave his owner’s name as John Dwa. The Kent News, in reporting the flight of this group, stated that eight of the enslaved people were owned by John Duyer. A John Dwyer appears in the Kent County census, but not as a slaveholder, suggesting that he may have hired some of these people, perhaps as a tenant on land owned by Chambers or Perkins, both of whom owned farms outside Chestertown.

None of those interviewed told Still about assistance they had received in Kent County. Yet they almost certainly had help; the number of enslaved people escaping at this time suggests a level of organization. The Kent News expressed concern over African Americans holding camp meetings. Such religious occasions allowed free blacks and enslaved people to meet, share information, and–slaveholders feared–organize resistance. In this instance, such fears may have been warranted. Individual free blacks were also accused of helping slaves escape. The Kent News reported in October that a black man had been jailed, charged with “abducting” slaves, and added that, “one thing is left for the slave-owners of this county–if this underground railroad is not put a stop to, we advise them to ship all their negroes to the South.” In December, another free black man, John Brown, was arrested for helping enslaved people escape.  

But authorities may have missed those who aided the Shephard group. Part of William Still’s network included an enslaved man, George Wilmer, who lived in the northeastern part of the county, and helped fugitives reach Thomas Garrett. Garrett reported that Wilmer had assisted some twenty-five people within four months alone. Graceanna Lewis, who sheltered the Shephard family, wrote to Still that the group left behind a black woman who knew of their plan and intended destination. This may have been Harriet Tillison, a free black woman who traveled the Upper Shore and was suspected of helping slaves escape. She was tarred and feathered by the same mob who attacked white abolitionist James Bowers in 1858. Alternatively, the woman Lewis refers to could have been a relative of the Shephards. There were several free black people in the county named Sheppard, including Margaret, who worked as a servant in the Chestertown household of George W.T. Perkins.  

I am indebted to the research of David Armenti, of the Legacy of Slavery website and to the Historical Society of Pennsylvania’s website, “Family Ties on the Underground Railroad,” for this story.

Image from William Still, The Underground Rail Road (1872)

Isaac Reed, 1856

Isaac Reed was enslaved by Board of Visitors and Governors member Dr. Benjamin F. Houston. (See Board; Apprenticeships.) In the summer of 1856, Reed, forty, escaped from Houston’s farm with Perry Shephard, enslaved on a nearby farm. The two men made their way north, eventually arriving at the office of the Philadelphia Underground Railroad operation run by William Still. Still recorded their arrival, but provided little detail about their escape or circumstances in slavery. Reed left behind a family: wife Hester Ann and children Philip Henry, Harriet Ann and Jane Elizabeth. Perhaps plans for them to accompany him fell apart. Enslaved people sometimes felt compelled to choose freedom over family.

Documents reveal several facts. In the 1860 census, Houston listed one fugitive, presumably Reed. The same census also shows Hester Reed, a free woman, forty, working as a laborer and living among a cluster of black families in the same area as Houston’s farm, with Harriett, age ten. Isaac Reed had moved on, literally and figuratively. The Canadian census of 1861 lists Reed in York, Ontario, and working as a shoemaker. He had a new wife, a fellow American named Rachael, probably also a former slave. By 1871, the Reeds had moved south to Hamilton. Exactly how Isaac Reed got to Canada is unknown, but William Still worked within a large network of abolitionists across Pennsylvania and New York who assisted enslaved people fleeing to Canada. Once they crossed the border, black churches and mutual aid societies as well as support from white abolitionists helped former American slaves start new lives.

I am indebted to the research of David Armenti, of the Legacy of Slavery website, on this story.


Harriet Fuller, 1859  

In 1859, yet another person Ezekiel Chambers enslaved, a woman named Harriet Fuller, ran away with her husband Cornelius. Cornelius Fuller was enslaved by a different master, a not uncommon situation in Maryland, where the average size of slaveholding was small, often resulting in family members being forced to live apart. We don’t know the details of how the Fullers made their way north. It is possible that they left hurriedly when they had an opportunity, because they left behind their thirteen-year-old daughter Kitty. We do know what Harriet Fuller said about Ezekiel Chambers: “He is no man for freedom, bless you. He owned more than any other man in that part of the country; he sells sometimes, and he hired out a great many; he would hire them to any kind of master, if he half killed you.”

Harriet and Cornelius Fuller reached Philadelphia where they were helped by William Still and his Underground Railroad network in making their way out of the country and eventually settling in St. Catharines, Ontario. They appear in the 1861 Canadian census, with Cornelius (age 34) listed as a laborer, Harriet (age 30) not employed. St. Catharines, on the western shore of Lake Ontario just across the border from Niagara Falls, was a market town with a population of about seven thousand, spurred by the building of the Welland Canal. It was known as a city of refuge for fugitives, who could find assistance from the Refugee Slaves’ Friends Society, an interracial group founded in 1852. One member was Harriet Tubman, who had escaped from Maryland’s Eastern Shore several years earlier. Tubman rented a house to shelter recent arrivals. Next door to Tubman’s house was the British Methodist Episcopal Church (Salem Chapel) where she worshipped; the church basement served a temporary shelter for recent arrivals. It is quite likely that the Fullers encountered Tubman, even worshipped with her, as the census lists them as members of the Episcopal Methodist Church.

What happened to Kitty Fuller is unknown. According to Still’s account, she was thirteen when her parents left Chestertown in 1859. Ezekiel Chambers’s 1860 census listing for Chestertown shows one enslaved girl aged fourteen and three girls aged fifteen, any of whom could be Kitty. 


With research contributed by Cassy Sottile, Class of 2019

Salem Chapel, St. Catharines, Ontario, where Harriet Tubman, and possibly Harriet and Cornelius Fuller, worshipped.